502-52-3Relevant articles and documents
Large-scale synthesis of both symmetrical and unsymmetrical triacylglycerols containing docosahexaenoic acid
Andrews, Philip C.,Fraser, Benjamin H.,Junk, Peter C.,Massi, Massimiliano,Perlmutter, Patrick,Thienthong, Neeranat,Wijesundera, Chakra
, p. 9197 - 9202 (2008)
A large-scale (~100 g) synthesis of symmetrical and unsymmetrical triacylglycerols containg docosahexaenoic acid (D) and two of either lauric (L), palmitic (P) or stearic acid (S) is described. Key improvements in purification of synthetic intermediates, in addition to a more efficient acetonide cleavage reaction affords the six TAGs (LaDLa, LaLaD, PDP, PPD, SDS, SSD) in yields of 80-90% and in regioisomeric purities greater than or equal to 90%.
Use of glycerol carbonate in an efficient, one-pot and solvent free synthesis of 1,3-sn-diglycerides
Kargar, Mojgan,Hekmatshoar, Rahim,Ghandi, Mehdi,Mostashari, Abdoljalil
, p. 259 - 264 (2013)
An efficient solvent-free synthesis of a variety of highly pure 1,3-sn-diglycerides (1,3-sn-diacylglycerols) in a two-step one pot process is described. Heating glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one) with fatty acid anhydrides 2a-d affords 1:1 mixtures of glycerol carbonate fatty esters 3a-3d and the corresponding fatty acids. Further heating the reaction mixtures in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 195-200 °C yields highly pure 1,3-sn-diglycerides 4a-4d.
Kumar,Billimoria
, p. 689,694 (1979)
LIPID PRODRUGS OF PREGNANE NEUROSTEROIDS AND USES THEREOF
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Paragraph 00281; 00284, (2020/02/23)
The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
LIPID PRODRUGS OF BTK INHIBITORS AND USES THEREOF
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Paragraph 00405; 00406; 00409, (2020/09/12)
The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
Discovery of FAHFA-Containing Triacylglycerols and Their Metabolic Regulation
Tan, Dan,Ertunc, Meric Erikci,Konduri, Srihari,Zhang, Justin,Pinto, Antonio M.,Chu, Qian,Kahn, Barbara B.,Siegel, Dionicio,Saghatelian, Alan
supporting information, p. 8798 - 8806 (2019/06/11)
FAHFAs are a class of bioactive lipids, which show great promise for treating diabetes and inflammatory diseases. Deciphering the metabolic pathways that regulate endogenous FAHFA levels is critical for developing diagnostic and therapeutic strategies. However, it remains unclear how FAHFAs are metabolized in cells or tissues. Here, we investigate whether FAHFAs can be incorporated into other lipid classes and identify a novel class of endogenous lipids, FAHFA-containing triacylglycerols (FAHFA-TGs), which contain a FAHFA group esterified to the glycerol backbone. Isotope-labeled FAHFAs are incorporated into FAHFA-TGs when added to differentiated adipocytes, which implies the existence of enzymes and metabolic pathways capable of synthesizing these lipids. Induction of lipolysis (i.e., triacylglycerol hydrolysis) in adipocytes is associated with marked increases in nonesterified FAHFA levels, demonstrating that FAHFA-TGs breakdown is a regulator of cellular FAHFA levels. To quantify FAHFA levels in FAHFA-TGs and determine their regioisomeric distributions, we developed a mild alkaline hydrolysis method that liberates FAHFAs from triacylglycerols for easier detection. FAHFA-TG concentrations are greater than 100-fold than that of nonesterified FAHFAs, indicating that FAHFA-TGs are a major reservoir of FAHFAs in cells and tissues. The discovery of FAHFA-TGs reveals a new branch of TG and FAHFA metabolism with potential roles in metabolic health and regulation of inflammation.